Anonymous wrote:I keep a running list of places I want to go, so if I think of something, or things come up in discussion with the kids, I add it to my list. It can be broad (like a country) or a specific hotel or activity that I read about. I crosswalk that with what I know about my kids--ie, one is a picky eater, one hates long hikes, one just wants to chill on the beach, etc so I can find things that will have something for everyone.
I plan as early as possible. As soon as the school calendar is approved I map out when we have extended weekends or other travel opportunities that aren't peak of peak. I keep Spring Break for visiting family (driving distance) because it's too expensive and crowded for me to deal with more exciting travel. I spend a good amount of time maximizing travel choices--but think carefully about the tradeoff between cost and convenience/time. So, for example, I will pay more for direct flights and I won't do red eyes; but I will spend a lot of time scouring flight options to find cheaper options. Same with lodging--and we often find airbnb or vrbo to be a better option (and can save on food, I actually like having some meals at home because a week of eating out makes me feel gross).
I have a "vacation" sub account on my high yield savings account. All my random "extra" money goes in there (tax refund, rebates, interest on savings accounts, credit card cash back, etc). I use that for guilt free vacation spending because it's completely outside of my regular budget. It adds up quicker than you'd think!
Oh--and one thing with planning early, I go back and check on my reservations periodically to make sure they're still the cheapest option. We had a reservation in Palm Springs last year, and they started renovating the lobby after I initially booked and reduced their rates. I was able to cancel and rebook and save $100 a night.